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Chapter 4

Organic Chemistry- Exam 2

QuestionAnswer
What are hydrocarbons? Compounds composed of hydrogen and carbon.
What does saturated mean for a hydrocarbon? It has only single bonds between carbons.
What is the parent chain in IUPAC naming? The longest consecutive chain of carbons.
If more than one parent chain is possible, which is chosen? The chain with the most substituents attached.
What prefix is added when the parent chain is cyclic? Cyclo-.
What ending do alkane substituents use? Substituents end in -yl instead of -ane.
When can a ring be a parent chain or a substituent? It depends on the number of carbons in the ring versus the attached chain
What ending do alkane substituents use? Start at the carbon attached to the parent chain and number within the substituent.
What is the basic rule for numbering one substituent? Number so the substituent receives the lowest possible locant.
How are multiple substituents handled when numbering? Give the first substituent the lowest possible number
What if the first substituent gives a tie? Choose the numbering that gives the second locant the lower number.
What is the final tie-breaker for numbering substituents? Give the lowest number alphabetically.
Do the same numbering rules apply to cycloalkanes? Yes.
How are identical substituents indicated? Use prefixes such as di-, tri-, tetra-, or penta-.
Are di-, tri-, and tetra- considered when alphabetizing? No; these prefixes are ignored.
What is the order for assembling an IUPAC name? Numbered substituents in alphabetical order, followed by the parent name.
What are conformations? Different 3-D shapes produced by rotation around single bonds.
What is a Newman projection? A view looking straight down a particular C–C bond.
How is the front carbon shown in a Newman projection? As a point.
How is the back carbon shown? As a large circle behind the front carbon.
What is a dihedral (torsional) angle? The angle between atoms on adjacent carbons.
Which ethane conformation is more stable? Staggered; it is lower in energy than eclipsed.
What causes torsional strain in an eclipsed conformation? Repulsion between eclipsing bonds/electron pairs.
Why is staggered ethane strongly favored? It has less torsional strain than the eclipsed form.
What causes extra strain in gauche butane? Steric strain between the two methyl groups.
Which butane arrangement is lower in energy: anti or gauche? Anti.
What is ring strain? The combination of angle strain and torsional strain.
What causes angle strain? Deviation of bond angles from the ideal angle caused by ring constraints.
What is the ideal bond angle for sp3 carbon? 109.5°.
Which cyclohexane conformation is most stable? The chair conformation.
Why is chair cyclohexane especially stable? It has 109.5° bond angles and staggered adjacent C–H bonds.
What are the two positions on a cyclohexane chair? Axial and equatorial.
How are axial bonds arranged around a chair? They point straight up and down, alternating around the ring.
What happens during a cyclohexane ring flip? Axial substituents become equatorial and equatorial substituents become axial.
Which position is more stable for a bulky substituent? Equatorial.
What causes axial steric strain in substituted cyclohexanes? 1,3-diaxial interactions.
How does substituent size affect axial crowding? Larger groups cause more steric crowding in the axial position.
What does cis mean for two cycloalkane substituents? They are on the same side of the ring.
What does trans mean for two cycloalkane substituents? They are on opposite sides of the ring
For a monosubstituted cyclohexane, which chair is favored? The chair with the substituent equatorial.
Created by: KristenR2025
 

 



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